Structural and functional insights into sulfated galactans: A systematic review

Glycoconjugate Journal

Volumn 27, Issue 1, 2010, Pages 1-12

  Pomin, Vitor H ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

Acrosome reaction; Agar; Carrageen; Marine organisms; Pharmacological application

Indexed keywords

ARABINOGALACTAN; CARRAGEENAN; DISACCHARIDE; FLUOROURACIL; GALACTAN; GALACTANE SULFATE; GALACTOSE; LAMBDA CARRAGEENAN; LAPSVS1; NU CARRAGEENAN; POLYSACCHARIDE; SULFATE; UNCLASSIFIED DRUG;

ACROSOME REACTION; ALGA; ANGIOSPERM; ANTICOAGULATION; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CELL WALL; CHEMICAL STRUCTURE; DRUG EFFECT; DRUG MECHANISM; FUNCTIONAL ASSESSMENT; HERPES SIMPLEX; HUMAN; INVERTEBRATE; LOW DRUG DOSE; NONHUMAN; PRIORITY JOURNAL; REVIEW; SEA URCHIN; SPECIES DIFFERENCE; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SULFATION; SYSTEMATIC REVIEW; VEIN THROMBOSIS;

ALGAE; ANIMALS; CARBOHYDRATE SEQUENCE; GALACTANS; GALACTOSE; MOLECULAR SEQUENCE DATA; PHYLOGENY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFATES;

ALGAE; ASCIDIACEA; CHONDRUS CRISPUS; ECHINOIDEA; INVERTEBRATA; MAGNOLIOPHYTA; PHYLA (ANGIOSPERM); UROCHORDATA;

EID: 77949275248     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-009-9251-z     Document Type: Review

References (58)

1. VP Pomin PA Mourão 2008 Structure, biology, evolution, and medical importance of sulfated fucans and galactans Glycobiology. 18 1016 1027 10.1093/glycob/cwn085 1:CAS:528:DC%2BD1cXhsVChtLrF 18796647
2. Pomin, V.P.: An overview about the structure-function relationship of marine sulfated homopolysaccharides with regular chemical structures. Biopolymers. 91, 601-609 (2009)
3. AP Alves B Mulloy JA Diniz PA Mourão 1997 Sulfated polysaccharides from the egg jelly layer are species-specific inducers of acrosomal reaction in sperms of sea urchins J. Biol. Chem. 272 6965 6971 10.1074/jbc.272.11.6965 1:CAS:528:DyaK2sXhvFKjsbo%3D 9054385 (Pubitemid 27166396)
4. Castro, M.O., Pomin, V.H., Santos, L.L., Vilela-Silva, A.C., Hirohashi, N., Pol-Fachin, L., Verli, H., Mourão, P.A.: A unique 2-sulfated beta-galactan from the EGG jelly of the sea urchin glyptocidaris crenularis: Conformation flexibility versus induction of the sperm acrosome reaction. J. Biol. Chem. (2009), in press
5. AC Vilela-Silva N Hirohashi PA Mourão 2008 The structure of sulfated polysaccharides ensures a carbohydrate-based mechanism for species recognition during sea urchin fertilization Int. J. Dev. Biol. 52 551 559 10.1387/ijdb.072531av 1:CAS:528:DC%2BD1cXht12qs7fP 18649269
6. PA Mourão 2007 A carbohydrate-based mechanism of species recognition in sea urchin fertilization Braz. J. Med. Biol. Res. 40 5 17 10.1590/S0100-879X2007000100002 17224991 (Pubitemid 46117714)
7. B Matsuhiro AF Conte EB Damonte AA Kolender MC Matulewicz EG Mejías CA Pujol EA Zúñiga 2005 Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta) Carbohydr. Res. 340 2392 2402 10.1016/j.carres.2005.08.004 1:CAS:528:DC%2BD2MXhtVCrsr3M 16125685 (Pubitemid 41375758)
8. LB Talarico RG Zibetti PC Faria LA Scolaro ME Duarte MD Noseda CA Pujol EB Damonte 2004 Anti-herpes simplex virus activity of sulfated galactans from the red seaweeds Gymnogongrus griffithsiae and Cryptonemia crenulata Int. J. Biol. Macromol. 34 63 71 10.1016/j.ijbiomac.2004.03.002 1:CAS:528: DC%2BD2cXkslWltbY%3D 15178011 (Pubitemid 38721187)
9. S Mazumder PK Ghosal CA Pujol MJ Carlucci EB Damonte B Ray 2002 Isolation, chemical investigation and antiviral activity of polysaccharides from Gracilaria corticata (Gracilariaceae, Rhodophyta) Int. J. Biol. Macromol. 31 87 95 10.1016/S0141-8130(02)00070-3 1:CAS:528:DC%2BD3sXmsFaitw%3D%3D 12559431 (Pubitemid 36143611)
10. ME Duarte DG Noseda MD Noseda S Tulio CA Pujol EB Damonte 2001 Inhibitory effect of sulfated galactans from the marine alga Bostrychia montagnei on herpes simplex virus replication in vitro Phytomedicine 8 53 58 10.1078/0944-7113-00007 1:CAS:528:DC%2BD3MXjsVWns7g%3D 11292240
11. ME Duarte JP Cauduro DG Noseda MD Noseda AG Gonçalves CA Pujol EB Damonte AS Cerezo 2004 The structure of the agaran sulfate from Acanthophora spicifera (Rhodomelaceae, Ceramiales) and its antiviral activity. Relation between structure and antiviral activity in agarans Carbohydr. Res. 339 335 347 10.1016/j.carres.2003.09.028 1:CAS:528:DC%2BD3sXhtVWhu7jN 14698892 (Pubitemid 38043939)
12. K Chattopadhyay T Ghosh CA Pujol MJ Carlucci EB Damonte B Ray 2008 Polysaccharides from Gracilaria corticata: sulfation, chemical characterization and anti-HSV activities Int. J. Biol. Macromol. 43 346 351 10.1016/j.ijbiomac. 2008.07.009 1:CAS:528:DC%2BD1cXhtFOksrfM 18694781
13. PJ Cáceres MJ Carlucci EB Damonte B Matsuhiro EA Zuñiga 2000 Carrageenans from chilean samples of Stenogramme interrupta (Phyllophoraceae): structural analysis and biological activity Phytochemistry 53 81 86 10.1016/S0031-9422(99)00461-6 10656412 (Pubitemid 30056851)
14. LB Talarico CA Pujol RG Zibetti PC Faría MD Noseda ME Duarte EB Damonte 2005 The antiviral activity of sulfated polysaccharides against dengue virus is dependent on virus serotype and host cell Antiviral. Res. 66 103 110 10.1016/j.antiviral.2005.02.001 1:CAS:528:DC%2BD2MXks1Cmt74%3D 15911027 (Pubitemid 40720115)
15. G Zhou Y Sun H Xin Y Zhang Z Li Z Xu 2004 In vivo antitumor and immunomodulation activities of different molecular weight lambda-carrageenans from Chondrus ocellatus Pharmacol. Res. 50 47 53 10.1016/j.phrs.2003.12.002 1:CAS:528:DC%2BD2cXjtVCgsrc%3D 15082028 (Pubitemid 38479667)
16. G Zhou H Xin W Sheng Y Sun Z Li Z Xu 2005 In vivo growth-inhibition of S180 tumor by mixture of 5-Fu and low molecular lambda-carrageenan from Chondrus ocellatus Pharmacol. Res. 51 153 157 10.1016/j.phrs.2004.07.003 1:CAS:528:DC%2BD2MXjvFKg 15629261 (Pubitemid 40040546)
17. G Zhou W Sheng W Yao C Wang 2006 Effect of low molecular lambda-carrageenan from Chondrus ocellatus on antitumor H-22 activity of 5-Fu Pharmacol. Res. 53 129 134 10.1016/j.phrs.2005.09.009 1:CAS:528:DC%2BD28XksFSi 16310373 (Pubitemid 43003479)
18. J Bürgermeister DH Paper H Vogl RJ Linhardt G Franz 2002 LaPSvS1, a (1 - >3)-beta-galactan sulfate and its effect on angiogenesis in vivo and in vitro Carbohydr. Res. 337 1459 1466 10.1016/S0008-6215(02)00163-5 12204607 (Pubitemid 35245433)
19. WR Farias AP Valente MS Pereira PA Mourão 2000 Structure and anticoagulant activity of sulfated galactans. Isolation of a unique sulfated galactan from the red algae Botryocladia occidentalis and comparison of its anticoagulant action with that of sulfated galactans from invertebrates J. Biol. Chem. 275 29299 29307 10.1074/jbc.M002422200 1:CAS:528:DC%2BD3cXmvFGqu7Y%3D 10882718 (Pubitemid 32043800)
20. MS Pereira FR Melo PA Mourão 2002 Is there a correlation between structure and anticoagulant action of sulfated galactans and sulfated fucans? Glycobiology 12 573 580 10.1093/glycob/cwf077 1:CAS:528:DC%2BD38XoslGqtbw%3D 12244069
21. MS Pereira AC Vilela-Silva AP Valente PA Mourão 2002 A 2-sulfated, 3-linked alpha-L-galactan is an anticoagulant polysaccharide Carbohydr. Res. 337 2231 2238 10.1016/S0008-6215(02)00215-X 1:CAS:528:DC%2BD38Xos1amtr8%3D 12433487 (Pubitemid 35335871)
22. MG Pereira NM Benevides MR Melo AP Valente FR Melo PA Mourão 2005 Structure and anticoagulant activity of a sulfated galactan from the red alga, Gelidium crinale. Is there a specific structural requirement for the anticoagulant action? Carbohydr. Res. 340 2015 2023 10.1016/j.carres.2005.05.018 1:CAS:528:DC%2BD2MXntVCksrw%3D 16023626 (Pubitemid 41033067)
23. PA Mourão 2004 Use of sulfated fucans as anticoagulant and antithrombotic agents: future perspectives Curr. Pharm. Des. 10 967 981 10.2174/1381612043452730 15078127 (Pubitemid 38380075)
24. PA Mourão MS Pereira 1999 Searching for alternatives to heparin: sulfated fucans from marine invertebrates Trends Cardiovasc. Med. 9 225 232 10.1016/S1050-1738(00)00032-3 11094330 (Pubitemid 30947869)
25. RJ Fonseca SN Oliveira FR Melo MG Pereira NM Benevides PA Mourão 2008 Slight differences in sulfation of algal galactans account for differences in their anticoagulant and venous antithrombotic activities Thromb. Haemost. 99 539 545 1:CAS:528:DC%2BD1cXnvVSkurk%3D 18327402
26. EH Farias VH Pomin AP Valente HB Nader HA Rocha PA Mourão 2008 A preponderantly 4-sulfated, 3-linked galactan from the green alga Codium isthmocladum Glycobiology 18 250 259 10.1093/glycob/cwm139 1:CAS:528: DC%2BD1cXjtFOitrg%3D 18174311 (Pubitemid 351359692)
27. MI Bilan EV Vinogradova AS Shashkov AI Usov 2007 Structure of a highly pyruvylated galactan sulfate from the Pacific green alga Codium yezoense (Bryopsidales, Chlorophyta) Carbohydr. Res. 342 586 596 10.1016/j.carres.2006. 11.008 1:CAS:528:DC%2BD2sXhtlWitrw%3D 17134684 (Pubitemid 46161416)
28. Love, J., Percival, E.: The polysaccharides of green seaweed Codium fragile: Part III A β-1,4-linked mannan. J. Chem. Soc. 3345-3350 (1964).
29. K Matsubara Y Matsuura A Bacic M-L Liao K Hori K Miyazawa 2001 Anticoagulant properties of a sulfated galactan preparation from a marine green alga Codium. Cylindricum. Biol. Macromol. 28 395 399 10.1016/S0141-8130(01) 00137-4 1:CAS:528:DC%2BD3MXivFegt7k%3D (Pubitemid 32372519)
30. HJ Bixler 1994 The carrageenan connection IV Brit. Food. J. 96 12 17 10.1108/00070709410060763
31. SH Knutsen DE Myslabodski B Larsen AI Usov 1994 A modified system of nomenclature for red algal galactans Bot. Mar. 37 163 169 10.1515/botm.1994.37. 2.163 1:CAS:528:DyaK2cXmsFKitL0%3D
32. M Lahaye 2001 Developments on gelling algal galactans, their structure and physico-chemistry J. Appl. Phycol. 13 173 184 10.1023/A:1011142124213 1:CAS:528:DC%2BD3MXkvVOmtLg%3D (Pubitemid 32489166)
33. AI Usov 1998 Structural analysis of red seaweed galactans of agar and carrageenan groups Food Hydrocoll. 12 301 308 10.1016/S0268-005X(98)00018-6 1:CAS:528:DyaK1cXnsF2mu7s%3D (Pubitemid 128155607)
34. F van de Velde L Pereira HS Rollema 2004 The revised NMR chemical shift data of carrageenans Carbohydr. Res. 339 2309 2313 10.1016/j.carres.2004.07.015 15337460 (Pubitemid 39165122)
35. RS Aquino AM Landeira-Fernandez A-P Valente LR Andrade PAS Mourão 2005 Occurrence of sulfated galactans in marine angiosperms: Evolutionary implications Glycobiology 15 11 20 10.1093/glycob/cwh138 1:CAS:528: DC%2BD2cXhtVKqu7nO 15317737 (Pubitemid 40202035)
36. JA Santos B Mulloy PA Mourão 1992 Structural diversity among sulfated alpha-L-galactans from ascidians (tunicates). Studies on the species Ciona intestinalis and Herdmania monus Eur. J. Biochem. 204 669 677 10.1111/j.1432-1033.1992.tb16680.x 1:CAS:528:DyaK38XhslSmtb0%3D 1311677
37. PA Mourão AS Perlin 1987 Structural features of sulfated glycans from the tunic of Styela plicata Chordata-Tunicata: A unique occurrence of L-galactose in sulfated polysaccharides Eur. J. Biochem. 166 431 436 10.1111/j.1432-1033.1987.tb13534.x 3609020
38. RM Albano MS Pavão PA Mourão B Mulloy 1990 Structural studies of a sulfated L-galactan from Styela plicata (Tunicate): Analysis of the Smith-degraded polysaccharide Carbohydr. Res. 208 163 174 10.1016/0008-6215(90) 80096-L 1:CAS:528:DyaK3MXmt1GqsQ%3D%3D 1964869
39. RH Whittaker 1969 New concepts of kingdoms of organisms Science 163 150 160 10.1126/science.163.3863.150 1:STN:280:DyaF1M%2Foslaksw%3D%3D 5762760
40. C Amornrut T Toida T Imanari E-R Woo H Park R Linhardt SJ Wu YS Kim 1999 A new sulfated beta-galactan from clams with anti-HIV activity Carbohydr. Res. 321 121 127 10.1016/S0008-6215(99)00188-3 1:CAS:528:DyaK1MXotVCqs7w%3D 10612006 (Pubitemid 29509711)
41. MSG Pavão RM Albano AM Lawsom PA Mourão 1989 Structural heterogeneity among unique sulfated L-galactans from different species of ascidians (tunicates) J. Biol. Chem. 264 9972 9979 2722889
42. MSG Pavão PA Mourão B Mulloy 1990 Structure of a unique sulfated alpha-L-galactofucan from the tunicate Clavelina Carbohydr. Res. 208 153 161 10.1016/0008-6215(90)80095-K 1964868
43. P Scudder PW Tanq EF Hounsell AM Lawson H Mehmet T Feizi 1986 Isolation and characterization of sulphated oligosaccharides released from bovine corneal keratin sulphate by the action of endo-beta-galactosidase Eur. J. Biochem. 157 365 373 10.1111/j.1432-1033.1986.tb09678.x 1:CAS:528:DyaL28Xktl2ruro%3D 2423331
44. VD Vacquier N Hirohashi 2004 Sea urchin spermatozoa Methods Cell Biol. 74 523 544 10.1016/S0091-679X(04)74021-2 1:CAS:528:DC%2BD2MXptVGlsg%3D%3D 15575620 (Pubitemid 39752510)
45. HJ Gunaratne GW Moy M Kinukawa S Miyata SA Mash VD Vacquier 2007 The 10 sea urchin receptor for egg jelly proteins (SpREJ) are members of the polycystic kidney disease-1 (PKD1) family BMC. Genomics. 8 235 10.1186/1471-2164-8-235 17629917
46. A Darszon JJ Acevedo BE Galindo EO Hernández-González T Nishigaki CL Treviño C Wood C Beltrán 2006 Sperm channel diversity and functional multiplicity Reproduction 161 977 988 10.1530/rep.1.00612 (Pubitemid 43904971)
47. 2+ channels in sperm function. In: Cell Calcium. 40:241-252 (2006)
48. CU de la Sancha G Martinez-Cadena J López-Godínez LE Castellano T Nishigaki A Darszon J García-Soto 2007 Rho-kinase (ROCK) in sea urchin sperm: Its role in regulating the intracellular pH during the acrosome reaction Biochem. Biophys. Res. Commun. 364 470 475 10.1016/j.bbrc.2007.10.050 17959147 (Pubitemid 350027798)
49. VD Vacquier WJ Swanson ME Hellberg 1995 What have we learned about sea urchin sperm bindin? Dev. Growth Differ. 37 1 10 10.1046/j.1440-169X.1995.00001. x 1:CAS:528:DyaK2MXnsFKnt7o%3D
50. RA Cameron TS Walkup K Rood JG Moore EH Davidson 1996 Specific in vitro interaction between recombinant Strongylocentrotus purpuratus bindin and a recombinant 45A fragment of the putative bindin receptor Dev. Biol. 180 348 352 10.1006/dbio.1996.0307 1:CAS:528:DyaK28XntlSqsb4%3D 8948597 (Pubitemid 26426181)
51. RW Glaser M Grüne C Wandelt AS Ulrich 1999 Structure analysis of a fusogenic peptide sequence from the sea urchin fertilization protein bindin Biochemistry 38 2560 2569 10.1021/bi982130e 1:CAS:528:DyaK1MXntVyktQ%3D%3D 10029551 (Pubitemid 29102818)
52. N Kamei CG Glabe 2003 The species-specific egg receptor for sea urchin sperm adhesion is EBR1, a novel ADAMTS protein Gene. Dev. 17 2502 2507 10.1101/gad.1133003 1:CAS:528:DC%2BD3sXotlWjtL0%3D 14561772 (Pubitemid 37271419)
53. KS Zigler 2008 The evolution of sea urchin sperm bindin Int. J. Dev. Biol. 52 791 796 10.1387/ijdb.072521kz 1:CAS:528:DC%2BD1cXht12qsL%2FI 18649291
54. N Hirohashi VD Vacquier 2002 Egg sialoglycans increase intracellular pH and potentiate the acrosome reaction of the sea urchin sperm J. Biol. Chem. 277 8041 8047 10.1074/jbc.M110661200 1:CAS:528:DC%2BD38XitFymsL8%3D 11777914 (Pubitemid 34968256)
55. JR Jackson MP Seed CH Kircher DA Willoughby JD Winkler 1997 The codependence of angiogenesis and chronic inflammation FASEB. J. 11 457 465 1:CAS:528:DyaK2sXjvFahsb8%3D 9194526
56. JW Fareed D Hoppensteadt RL Bick 2000 An update of heparins at the beginning of the new millennium Sem. Thromb. Haemost. 26 5 21 10.1055/s-2000-9498 1:CAS:528:DC%2BD3cXntV2hs7g%3D
57. M Guerrini D Beccati Z Shriver A Naggi K Viswanathan A Bisio I Capila JC Lansing S Guglieri B Fraser A Al-Hakim NS Gunay Z Zhang L Robinson L Buhse M Nasr J Woodcock R Langer G Venkataraman RJ Linhardt B Casu G Torri R Sasisekharan 2008 Oversulfated chondroitin sulfate is a contaminant in heparin associated with adverse clinical events Nat. Biotechnol. 10 1 7
58. TK Kishimoto K Viswanathan T Ganguly S Elankumaran S Smith K Pelzer JC Lansing N Sriranganathan G Zhao Z Galcheva-Gargova A Al-Hakim GS Bailey B Fraser S Roy T Rogers-Cotrone L Buhse M Whary J Fox M Nasr GJ Dal Pan Z Shriver RS Langer G Venkataraman KF Austen J Woodcock R Sasisekharan 2008 Contaminated heparin associated with adverse clinical events and activation of the contact system New. Engl. J. Med. 358 2457 2467 10.1056/NEJMoa0803200 1:CAS:528:DC%2BD1cXmvFKmtb4%3D 18434646 (Pubitemid 351793019)